HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(-)-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1-(5-Methyl-1,2,4-oxadiazol-3-yl)ethan-1-amine | HCID 43559295 | — |
| Reactant | 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid | HCID 71087346 | — |
| Solvent | Heptane | HCID 8900 | — |
| Product | 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(-)-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide | HCID 78010149 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42a) and α,5-dimethyl-1,2,4-oxadiazole-3-methanamine (CAN 1153834-40-2) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/20% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 98.1%, 343.1767 (M+H)+, αD20 (MeOH)=−28.2°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09290451B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-6fa039b92dd84b0d995efe76415b8cb7 |
| Source note | uspto-grants-2016_03 |